Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester
• CAS No.: 188123-37-7
• Molecular Formula: C₁₅H₁₅NO₄
• Molecular Weight: 273.288

Synonyms:Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

Chemical Property of Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

There total 4 articles about Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-36-6) → Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-37-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 7h; Heating;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-one (139240-75-8) → Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-37-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / Et₃N, DMAP / tetrahydrofuran / 1 h / Ambient temperature

2: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

3: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

4: 81 percent / AIBN, Bu₃SnH / benzene / 7 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(1S,2R,6S,7R)-4-Oxo-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-8-ene-5-carboxylic acid tert-butyl ester (188123-34-4) → Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-37-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

2: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

3: 81 percent / AIBN, Bu₃SnH / benzene / 7 h / Heating

With 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(96)02402-1

upstream raw materials:

Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-8-en-4-one

(1S,2R,6S,7R)-4-Oxo-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-5-carboxylic acid tert-butyl ester

Benzoic acid (1S,2R,3S,4R)-3-tert-butoxycarbonylamino-bicyclo[2.2.1]hept-5-en-2-yl ester

Downstream raw materials:

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-hexanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-heptanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-2-methyl-pent-4-enoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

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